1-Aminopiperidine → HCID 20232079, compound

HRID 2290338Notes

Reaction equation

HRID 2290338 reaction equation
C([Li])CCC.[NH2:6][N:7]1[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1.[CH3:13][C:14]1[N:15]=[C:16](S(C)(=O)=O)[N:17]=[N:18][C:19]=1[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>O1CCCC1>[CH3:13][C:14]1[N:15]=[C:16]([NH:6][N:7]2[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]2)[N:17]=[N:18][C:19]=1[C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

Participants

5

Reactant 3

HCID 166581-AminopiperidineHCID 20232078HCID 20232078, compoundHCID 178418339Butyllithium

Product 1

HCID 20232079HCID 20232079, compoundYield 41.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

n-Butyllithium (25 g/250 ml solution in hexane) (28.5 ml) was added dropwise to a stirred solution of N-aminopiperidine (4.12 g) in tetrahydrofurane (40 ml) at -78° C. and the stirring was continued for 2 hours at room temperature. A solution of 5-methyl-3-methylsulfonyl-6-phenyl-1,2,4-triazine (5 g) in tetrahydrofuran (100 ml) was added dropwise to the above obtained solution at -78° C. in 70 minutes with stirring and the stirring was continued for 30 minutes at the same temperature. The reaction mixture was washed with water and brine, and then extracted with ethyl acetate. The extract was washed with brine, dried over sodium sulfate and evaporated. The resulting residue was dissolved in chloroform and extracted with an aqueous solution of 6N-hydrochloric acid. The extract was made alkaline with an aqueous solution of potassium carbonate and extracted with ethyl acetate. The extract was washed with water, dried over sodium sulfate, and evaporated. Thus obtained crude product (3.82 g) was purified by chromatography on silica gel (100 g) using a mixture of benzene and ethyl acetate (2:1) as an eluent and recrystallized from diisopropyl ether to give crystals of 5-methyl-6-phenyl-3-piperidinoamino-1,2,4-triazine (2.25 g).

Workup

  1. waitthe stirring was continued for 30 minutes at the same temperature
  2. washThe reaction mixture was washed with water and brine
  3. extractionextracted with ethyl acetate
  4. washThe extract was washed with brine
  5. dry with materialdried over sodium sulfate
  6. customevaporated
  7. dissolutionThe resulting residue was dissolved in chloroform
  8. extractionextracted with an aqueous solution of 6N-hydrochloric acid
  9. extractionextracted with ethyl acetate
  10. washThe extract was washed with water
  11. dry with materialdried over sodium sulfate
  12. customevaporated
  13. customThus obtained crude product (3.82 g)
  14. customwas purified by chromatography on silica gel (100 g)
  15. additiona mixture of benzene and ethyl acetate (2:1) as an eluent
  16. customrecrystallized from diisopropyl ether

Sources & evidence

ORD record
ord-f6d06884d6dc48f29af384fa379e67c0
Source dataset
uspto-grants-1986_10
Patent number
US04616014

Reaction notes

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